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General Description

7-Methoxy-2-phenyl-1H-indole is a chemical compound with the molecular formula C15H13NO. It is a derivative of indole and belongs to the class of organic compounds known as tryptamines. 7-Methoxy-2-phenyl-1H-indole is commonly used in the field of medicinal chemistry for its potential pharmacological properties, particularly in the development of pharmaceutical drugs. Tryptamines have been studied for their various effects on the central nervous system, including psychoactive and hallucinogenic properties. 7-METHOXY-2-PHENYL-1H-INDOLE is also of interest in research related to serotonin receptors and their involvement in psychiatric and neurological disorders. Further studies are needed to fully understand its potential therapeutic significance and biological activity.

Upstream product

• 90-04-0 2-methoxy-phenylamine 
• 70-11-1 α-bromoacetophenone 
• 496043-85-7 2-[2'-(N-Boc-N-trimethylsilyl-amino)-3'-methoxyphenyl]-1,3-dithiane 
• 861631-65-4 3-methoxy-2-nitro-1-[(E)-2-phenylvinyl]benzene 
• 358657-78-0 2-(3'-methoxy-2'-nitrophenyl)-1,3-dithiane 
• 731797-79-8 (E)-2-methoxy-N-(1-phenylethylidene)aniline 
• 536-74-3 phenylacetylene 
• 50868-73-0 2-methoxy-6-methylbenzeneamine 
• 98-88-4 benzoyl chloride 
• 98-86-2 acetophenone 
• 20768-48-3 2-methoxy-N-(1-phenylethylidene)benzenamine 
• 529-28-2 4-iodoanisol 
• 7654-06-0 3-phenyl-2H-azirine 
• 396094-82-9 2-[2'-(N-Boc-amino)-3'-methoxyphenyl]-1,3-dithiane 

Downstream Products

• 3177-80-8 2-amino-3-methoxybenzoic acid 
• 857599-33-8 2-(benzoyl-methyl-amino)-3-methoxy-benzoic acid 
• 485-27-8 3-methoxy-2-methylamino-benzoic acid 
• 857193-93-2 2-benzoylamino-3-methoxy-benzoic acid 
• 500893-17-4 N-(2-formyl-4-methoxyphenyl)benzamide 
• 857764-45-5 7-methoxy-1-methyl-2-phenyl-1H-indole 

Relevant academic research and scientific papers

Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles

An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.

New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer

We designed 39 new 2-phenylindole derivatives as potential anticancer agents bearing the 3,4,5-trimethoxyphenyl moiety with a sulfur, ketone, or methylene bridging group at position 3 of the indole and with halogen or methoxy substituent(s) at positions 4-7. Compounds 33 and 44 strongly inhibited the growth of the P-glycoprotein-overexpressing multi-drug-resistant cell lines NCI/ADR-RES and Messa/Dx5. At 10 nM, 33 and 44 stimulated the cytotoxic activity of NK cells. At 20-50 nM, 33 and 44 arrested >80% of HeLa cells in the G2/M phase of the cell cycle, with stable arrest of mitotic progression. Cell cycle arrest was followed by cell death. Indoles 33, 44, and 81 showed strong inhibition of the SAG-induced Hedgehog signaling activation in NIH3T3 Shh-Light II cells with IC50 values of 19, 72, and 38 nM, respectively. Compounds of this class potently inhibited tubulin polymerization and cancer cell growth, including stimulation of natural killer cell cytotoxic activity and repression of Hedgehog-dependent cancer.

Pd(II)/Bu4NBr/DMSO catalytic system for practical synthesis of indoles and pyrroles from imines through aerobic dehydrogenative cyclization

N-Aryl- and N-allylimines derived typically from substituted acetophenones undergo palladium(II)-catalyzed dehydrogenative cyclization reactions in the presence of tetrabutylammonium bromide and molecular oxygen in DMSO to afford indole and pyrrole deriva

PROCESSES FOR PREPARING INDOLES

Methods for the synthesis of an indole in provided. Methods comprise oxidizing a N-aryl imine in the presence of a palladium-based catalyst, an oxidant, and a solvent.

Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: Indole synthesis from anilines and ketones

We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.

Electrosynthesis of substituted 1H-indoles from o-nitrostyrenes

A novel procedure has been devised for the synthesis of derivatives of 1H-indole that is based on the direct, room-temperature electrochemical reduction of substituted o-nitrostyrenes at carbon cathodes in N,N-dimethylformamide containing tetramethylammonium tetrafluoroborate as supporting electrolyte and in the presence of a 10-fold molar excess of a proton donor (phenol or methyl 3-oxobutanoate).

Exploiting the chemistry of strained rings: Synthesis of indoles via domino reaction of aryl iodides with 2 H-azirines

(Equation Presented). The highly strained 2H-azirine ring system has been the source of considerable theoretical and synthetic work. The reaction of these strained heterocycles with transition metals has been documented to give rise to ring opening and subsequent formation of varied heterocycles. An interesting domino reaction is described wherein the strained bicyclic alkene, norbornene, mediates the reaction of 2H-azirines with aryl iodides under palladium catalysis to provide indole or polycyclic dihydroimidazole heterocycles.

Microwave-assisted, solvent-free Bischler indole synthesis

The solid-state reaction between anilines and phenacyl bromides in the presence of an equimolecular amount of sodium bicarbonate gives N-phenacylanilines. Microwave irradiation of mixtures of these compounds with anilinium bromides at 540 W for 45-60 s provides a mild, general, and environmentally friendly method for the synthesis of 2-arylindoles in 50-56% overall yields. A one-pot variation of the method, involving irradiation of 2:1 mixtures of anilines and phenacyl bromides, was also developed, allowing a simplified experimental procedure and leading to improved yields (52-75%). Georg Thieme Verlag Stuttgart.

A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions

A mild and efficient method for the palladium-catalyzed reductive cyclization of ortho-nitrostyrenes to afford indoles is reported. Treatment of ortho-nitrostyrenes with 0.1 mol% palladium (II) trifluoroacetate [Pd(TFA) 2] and 0.7 mol% 3,4,7,8-tetramethyl-1,10-phenanthroline (tm-phen) in DMF at 15 psig CO and 80°C afforded indoles in good to excellent yields. When the reaction was conducted in toluene, the corresponding N-hydroxyindole was isolated. A mechanism that accounts for the formation of N-hydroxyindole is proposed.

Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase

Titanium(IV) benzylidenes bearing a masked oxygen or nitrogen nucleophile in the ortho position were generated from thioacetals, using low-valent titanocene complex, Cp2Ti[P(OEt)3]2. Methylene acetal, alkyl ether, silyl ether, fluoro, tertiary amino, and N-alkyl, N-benzyl, N-prenyl, and N-silyl tert-butyl carbamate groups were tolerated in the titanium alkylidene reagents (Schrock carbenes). Aryl-chlorine bonds were stable to the titanium benzylidene functionality, but there was poor chemoselectivity for the reduction of the thioacetal in the presence of an aryl chloride. The titanium benzylidenes converted Merrifield and Wang resin-bound esters into enol ethers. The oxygen nucleophile was masked as a TMS ether, and when the resin-bound enol ethers bearing this ortho substituent were treated with 1% TFA in dichloromethane, benzofurans were released from resin in high yields. The chameleon catch strategy ensured excellent purity. In a similar way, N-alkylated and N-silylated tert-butyl carbamates were used for the synthesis of N-alkyl and N-Boc indoles, respectively. These traceless solid-phase syntheses of heterocycles are believed to involve post-cleavage modification rather than cyclative termination.